1,3-Dichloroacetone → 2-chloromethyl-6-(4-fluoro-phenyl)-6H-imidazo[1,2-c]pyrimidin-5-one

HRID 538226Notes

Reaction equation

HRID 538226 reaction equation
[Cl:1][CH2:2][C:3]([CH2:5]Cl)=O.[NH2:7][C:8]1[CH:13]=[CH:12][N:11]([C:14]2[CH:19]=[CH:18][C:17]([F:20])=[CH:16][CH:15]=2)[C:10](=[O:21])[N:9]=1>CN(C=O)C>[Cl:1][CH2:2][C:3]1[N:7]=[C:8]2[CH:13]=[CH:12][N:11]([C:14]3[CH:19]=[CH:18][C:17]([F:20])=[CH:16][CH:15]=3)[C:10](=[O:21])[N:9]2[CH:5]=1

Participants

4

Reactant 2

HCID 107931,3-DichloroacetoneHCID 682901544-amino-1-(4-fluoro-phenyl)-1H-pyrimidin-2-one

Product 1

HCID 682908442-chloromethyl-6-(4-fluoro-phenyl)-6H-imidazo[1,2-c]pyrimidin-5-oneYield 75.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
150 °C

Procedure

1,3-Dichloroacetone (2.27 g, 11.92 mmol) was added to a solution of 4-amino-1-(4-fluoro-phenyl)-1H-pyrimidin-2-one (4.6 g, 12 mmol) in DMF (135 mL). The mixture was stirred at 150° C. for 30 minutes under microwave irradiation and then the solvent was evaporated in vacuo. The crude product was purified by flash column chromatography (silica; AcOEt in DCM with a gradient of 0/100 to 30/70). The desired fractions were collected and the solvents evaporated in vacuo to yield 2-chloromethyl-6-(4-fluoro-phenyl)-6H-imidazo[1,2-c]pyrimidin-5-one (2.5 g, 75% yield) as a solid.

Workup

  1. customthe solvent was evaporated in vacuo
  2. customThe crude product was purified by flash column chromatography (silica
  3. customThe desired fractions were collected
  4. customthe solvents evaporated in vacuo

Sources & evidence

ORD record
ord-940f3e0007c74c13a5a0308c5fb5cf79
Source dataset
uspto-grants-2014_10
Patent number
US08865725B2

Reaction notes

Loading…